Ethyl bromoacetate → Ethyl (1-allylhydrazino)acetate

HRID 718878Notes

Reaction equation

HRID 718878 reaction equation
[CH2:1]([NH:4][NH2:5])[CH:2]=[CH2:3].C(N(CC)CC)C.Br[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]>ClCCl.C(OCC)(=O)C>[CH2:1]([N:4]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[NH2:5])[CH:2]=[CH2:3]

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 8471TriethylamineHCID 81921Allylhydrazine

Product 1

HCID 45082254Ethyl (1-allylhydrazino)acetateYield 87%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To the solution of 70%-allylhydrazine 7.73 g (75 mmol) and triethylamine 8.38 ml (60 mmol), ethyl 2-bromoacetate in dichloromethane 25 ml was added and stirred at room temperature for 24 hours and reflux for additional 1 hour. The reaction mixture was diluted with ethyl acetate 150 ml and washed with brine 100 ml. The organic phase was dried with magnesium sulfate and filtered and the mother solution was concentrated in vacuo to obtain the title compound 6.90 g (87%).

Workup

  1. temperaturereflux for additional 1 hour
  2. washwashed with brine 100 ml
  3. dry with materialThe organic phase was dried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationthe mother solution was concentrated in vacuo

Sources & evidence

ORD record
ord-6fc8cbf2a7b640028a6ed2d9e45785e4
Source dataset
uspto-grants-2015_11
Patent number
US09193734B2

Reaction notes

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